


Staying Late

by OswinTheStrange



Category: Supernatural
Genre: AU, Cunnilingus, F/F, Fingering, Making Out, Office Sex, Secretary!Reader, boss!Rowena
Language: English
Status: Completed
Published: 2018-02-23
Updated: 2018-02-23
Packaged: 2019-03-23 02:06:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,587
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13777416
Author URL: https://archiveofourown.org/users/OswinTheStrange/pseuds/OswinTheStrange
Summary: Reader is Rowena's MacLeod's secretary/personal assistant who stays late when her boss does. One night, her boss summons her to her office for a little help.





	Staying Late

You stifled a yawn as you glanced at the clock. It was past nine. You should be home now, curled up on the couch binging something on Netflix. Normally, you were, but when the boss stayed late, so did her loyal personal assistant a.k.a. you. There wasn't even any real reason to, except for getting her coffee when she said she needed some.

You glanced through the cracked door to your boss's office. She was on her computer, eyes focused on the screen, her brows furrowed in concentration. A strand of red hair fell in her face, but it was quickly whisked away and smoothed back in one graceful movement.

You looked away, before what you were doing could be considered staring, and back out into the empty office. Everyone else had left by seven, leaving the office totally silent except for the ticking of the clock. It made you a bit uneasy. You wondered if you'd get in trouble for taking out you phone and listening to some music. Surely, as long as you could hear your boss if she called you for anything, it would be alright?

You glanced back into her office. She was biting her lip now. You stared, subconsciously biting your own. Her eyes began to move towards the door and you quickly moved out of sight, blushing heavily. It wasn't the first time you'd watched her. You sometimes felt a bit like a creep for doing it, but you couldn't help it. 

Rowena MacLeod was absolutely gorgeous. And with her sexy accent and air of untouchable confidence, you were immediately drawn to her. Working for her and getting to know her only made your 'crush' grow. She was a shrewd business woman and not easily intimidated. But she was also a good boss. A little demanding, yes, but was at least fair and treated everyone equally. Even the higher ups didn't get special treatment from her and she'd at least listen if someone had a genuine complaint (although, they'd get promptly kicked out of her office if they were wasting her time). She wasn't above the occasional compliment, either. She'd once said that you were the best assistant she'd had because you always did exactly as she said. Of course, that was only because you hung onto her every word, but you'd politely thanked her and said no more.

But as much as you admired her, you knew it would never happen, so you spent half your time hoping she didn't notice your crush. You almost felt that was impossible, because she seemed to notice everything, but maybe this was one thing she didn't pay attention to. You certainly hoped so.

You leaned down, grabbed your bag from the floor, and searched it for your phone. Just as your hand touched it, a voice interrupted you.

"Y/N, I need you in here," Rowena called.

Well, at least you were finally, hopefully, going to be given something to do. Setting your purse back down, you stood and walked over to her office, pushing the door open. "Yes, ma'am?"

"You're good with computers, right?" she asked.

"Um, sort of. I'm no genius, but if there's a problem I can try-" you said.

"Good," she set, cutting you off. "My computer just stopped working. I need you to take a look."

"Oh, um, that actually sounds like more than I know how to-" you tried.

"Just take a look. I doubt there's anywhere I can take it this late at night," she said.

"Oh, um, okay," you said, stepping inside.

"And close the door behind you," she instructed.

You did so, the click sounding loudly throughout the quiet office. You walked towards the desk, heart beating nervously. Could she hear it? Once you were close enough, she got out of her chair, motioning for you to sit down.

You sat down, trying to focus on the task you'd been given, and trying to calm your racing heart. Rowena stood very close by, her breath warming your neck. You could smell her perfume from where you were.  _No, focus_! you told yourself.

Doing the most basic thing you could think of, you pressed the power button. Nothing. You felt around the frame and keyboard. It was a little warm, but nothing serious, so no overheating. "Maybe the battery died?" you suggested. "If you've had it long enough, it's going to die, no matter how good your laptop condition is."

And the computer was in  _very_  good condition. It still looked new.

"I've had it just over a year," Rowena said. "It can't have died that quickly."

"No, probably not," you agreed. You glanced around, trying to think of something else you could do. You really didn't want to fail. You wanted to figure this out, to impress Rowena. Or, at least satisfy her, since you doubted whatever you did would be very impressive.

Your eye passed over the charger, and you realized what was wrong. "I found the problem," you said, plugging the charger back into the computer. "The charger must have fallen out."

"I wonder how that happened?" Rowena said. But she didn't sound at all confused or relieved in anyway. It sounded... almost smug.

"Give it a minute and it should be fine. I hope you saved whatever you were working on, though," you said, moving to stand.

A hand was placed on your shoulder, pushing you back down. "And what if I didn't? Is there a way to bring it back?" Rowena asked. She leaned in closer, her mouth next to your ear.

"M-Maybe. I mean, um, I've heard of a way for documents on Word, I think, but I can't remember it. I could check Google for it, but if it's anything serious, I'd wait until tomorrow and have someone from IT help. I wouldn't want to mess anything up," you stammered.

"Oh, I'm sure it will be fine," she said. Her voice was a low purr and it sent tingles up and down your spine. "But I brought you in for another reason. There's something I wanted to discuss with you."

"Discuss?" you asked, fighting to keep your voice from cracking.

"Mmhm," she hummed. "See, I'm  _very_  good at noticing things, and you're  _very_  bad at hiding them."

You froze, fear paralyzing you. Oh, shit.

"And I've noticed your little attraction to me," she continued.

Immediately, you began apologizing. "I'm so sorry, I didn't mean to-"

Rowena stepped in front of you, placing a finger over your lips as she shushed you. "There's no need to apologize, dear. It hasn't escaped my notice that you're quite attractive yourself."

"Me?" you squeaked. You'd never thought of yourself as attractive. You didn't think of yourself as horribly ugly, either, but attractive wasn't a word you'd ascribe to yourself. You were just sort of average.

Rowena smirked. "Yes, you. Now, you have two options," she said, trailing her fingers down your throat to rest on your shoulder again. "You can say 'no' and this will stop. You can go home and we'll forget about tonight. Or, you can say 'yes' and we'll go as far as you'd like."

The two options ran through your head at light speed. As much as you wanted to say yes, to shout it from the rooftops, no was a tempting option. There were so many reasons why you should say no. She was your boss. This could be considered an abuse of power. Someone might come back for something they forgot, or the janitors might come through soon. You weren't very experienced and would probably be lousy, which would be completely embarrassing and not enjoyable for either of you.

But every cell in your being wanted yes, was screaming yes. The opportunity was far too good to give up. "Yes," you breathed.

Rowena's smirk grew, like the cat that got the canary. "Wonderful," she purred. Instantly, her lips were on yours, and any hesitance drained away. They were warm and soft and moved expertly against your own. You kissed back, trying to find the rhythm, and then sinking in perfectly when you did. She straddled you, her hands going to your waist as her tongue probed at your lips. You opened your mouth, letting her slip inside as your hands went to her biceps. She was surprisingly more muscular than she looked.

You had no idea what you were doing, so you let her lead. Well, it was less of you  _letting_  her take the lead than you just not trying to take control. You doubted anyone could  _let_  Rowena MacLeod do anything. If she wanted to do something, she did it. And right now, that was you, and you were perfectly fine with that.

Her hands moved up from your waist to your breasts, squeezing gently. You didn't even realize you'd let out a moan until a few seconds after. You blushed heavily and Rowena chuckled, breaking the kiss to move her lips to your neck.

You let out a gasp when her lips found your pulse point, nipping it gently and then sucking it. Her hands moved from your breasts, undoing the buttons of your shirt, her mouth moving lower and lower with each button until she reached your breasts. She pushed your shirt off your shoulders and you slid your arms out. Your bra quickly followed the shirt, freeing your breasts. Rowena's office was normally kept cool, and the chill air made your nipples harden and stand out. You blushed and instinctively moved to cover them, but Rowena stopped you, gently grasping your wrists. "There's no need to by shy," she said, giving you an encouraging smile. Still blushing, you nodded and lowered your arms, and immediately the cold air was replaced by the warmth of her mouth and hands. A groan slipped past your lips.

"You like this?" Rowena asked smugly, releasing your nipple.

You nodded, panting.

"Use your words, darling," she said.

"Y-Yes," you gasped.

She smirked, watching you carefully. "Then you're going to love this," she said.

She slipped from the chair, kneeling on the floor as her mouth and hands moved down your body. Once her hands reached your waist band, she was pulling down your skirt. You quickly assisted her, lifting up so she could pull it off of you and toss it several feet away. A hand slipped between your legs, gently rubbing over your panties. Your eyes fluttered shut and you let your head fall back, enjoying the feeling.

A minute later, Rowena grew tired of teasing you and your panties quickly followed your skirt. "You're absolutely soaked," she breathed. "Is this all for me?"

You nodded, glancing down her at her. She had a wicked smile on her lips as she stared mischievously as you. Looking you directly in the eye, she leaned forward and gave you a long, slow lick. Your head fell back again as you let out a soft moan.

She continued licking you, the movements of her tongue getting shorter but faster, and moving to focus more and more on your clit. A finger circled your entrance before slipping inside. You let out a quiet moan as it gave a few experimental thrusts before a second finger was added. Each movement, each touch, brought you higher and higher. You alternated between letting your head fall back and lifting it to watch Rowena as she worked you closer and closer to orgasm. Each time she'd meet your eyes, she'd watch you carefully, eyes devouring the sight of you as you squirmed and moaned under her skilled fingers and tongue.

Within another few minutes, you were undone. It started as heat pooling in your core, then it grew larger and hotter until it exploded, streaming through your body like electricity. You cried out and called Rowena's name, back arching as your fingers dug into the armrests of her chair.

Rowena worked you through it, helping you come down from your high as you gasped and moaned. Her moments slowed, and eventually stopped altogether. She pulled her fingers from you with a wet noise that was surprisingly loud in the quiet office. You watched with half-shut eyes as she licked her fingers clean. Her lips glistened with your slick, but before she could lick them you leaned down, pulling her into a rough kiss. You both moaned, hands grabbing everywhere, and she moved to straddle you again.

Your hands moved around her body, and then lower. You wanted to make her feel as good as she'd made you. You wanted to watch her come apart as she had watched you. You wanted to hear her moans and whimpers, wanted to know that it was you who was causing her such pleasure. Your hands unbutton her blouse, taking care not to damage it, even though all you wanted was to rip it off. You didn't bother pulling her blouse or bra off. You were too impatient, and instead just pulled down the bra as far as it would go with her shirt still in the way. Your lips latched around her nipple, licking and sucking, occasionally biting. Rowena moaned, her hands tangling in your hair. Your hands snaked down to her pants, undoing them and slipping a hand inside. You gasped when you felt only bare skin.

You glanced up at her and she shrugged. "I was hoping you were going to say yes to this," she said.

"So how long have you had this planned?" you asked. You slid your fingers along her pussy, feeling how wet she was. "Fuck."

"A while now," she said. "I've just been working out the details and watching to see just how far your attraction went." She let out a soft gasp at your touch.

You pressed more firmly, coating your fingers in her juices before slipping a finger inside her. Rowena let out a louder gasp, following by a groan. "Oh, yes!"

You smiled and added another finger, then began moving them faster. Your thumb circled her clit, almost touching, but not quite.

Rowena began moving her hips, riding your fingers as you thrust them in and out of her. "Oh, fuck! Yes!" She was far more vocal than you had been and much louder. You were glad everyone else had gone home, because otherwise you were sure they'd be able to hear  _everything_. Your thumb settled right on her clit while you added a third finger, moving your fingers faster.

A few minutes later, she shook and trembled, crying out as her orgasm hit her. Just as she had done for you, you worked her through it, continuing until her hips stopped and she whimpered, moving away from your hand.

You slid your hand out of her. In the low office light, your fingers glistened. You slipped them into your mouth, licking them clean and moaning.

"For someone so shy, you certainly know what you're doing," Rowena panted.

"I learn fast. And I had a good teacher," you said, smirking at her.

Rowena returned the smirk. "I have a few things at home I need help with. Would you be interested in assisting me?" 

"That depends. Will you need me to stay late with you any other nights?" you asked.

"Oh, yes. Quite often, too, for the foreseeable future," she said.

"Then my answer is yes, I'd love to 'assist' you at your home," you said. The two of you shared a look. You were certainly going to enjoy staying late from now on.

**Author's Note:**

> Thanks to my editor, Marrilyn, whose comments give me life!  
> Hope ya'll enjoy!


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